A kind of synthetic method of optically pure cloprostinol
The technology of a chloroprostol and a synthesis method, which is applied in the synthesis field of optically pure chloroprostol, can solve the problems of complicated preparation method and low yield of dextro-chloroprostol, and achieves short reaction steps, high optical purity, and low reaction time. Handling simple effects
Active Publication Date: 2020-04-17
厦门欧瑞捷生物科技有限公司
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[0007] For solving the complex preparation method of d-cloprostinol in the above-mentioned background technology, the problem of low yield, the invention provides a kind of synthetic method of optically pure cloprostinol, comprising the following steps:
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[0038] The invention provides a kind of synthetic method of optically pure cloprostinol, comprising the following steps:
[0039] Step a, add L-cory lactone diol and oxidizing agent to the solvent, and under the action of DMN-AZADO catalyst, carry out selective oxidation reaction, quench, extract, wash, dry, and filter to obtain aldehyde-containing Cory Lactone monoalcohol, namely compound I;
[0040] The process route is as follows:
[0041]
[0042] Specifically, after performing the selective oxidation reaction, adding saturated Na 2 S 2 o 3The solution was quenched, the aqueous phase was extracted with dichloromethane, the combined organic phases were washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and filtered to obtain a dichloromethane solution of compound I for use in step b.
[0043] Step b, carry out olefination reaction of compound I, phosphonate and solvent under the catalysis of lithium hydroxide, quench, extract, wash, ...
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The invention relates to the technical field of medicine preparation, in particular to a synthesizing method of optical pure cloprostenol. The synthesizing method comprises the steps: levogyration corey lactone diol is adopted as a raw material and subjected to oxidization, olefin, reduction and Wittig reactions, and a compound IV is prepared; then (s)-phenylethylamine is used for a separation reaction and recrystallization; and after a compound V is obtained and subjected to acidification adjustment, the optical pure cloprostenol is obtained. Compared with an existing synthesizing method, thelevogyration corey lactone diol which is cheap and easy to obtain is directly adopted as the raw material, hydroxyl does not need to be selectively protected, primary alcohol is directly oxidized selectively, and a synthesizing reaction is carried out; the reaction steps are short, the optical purity of a target product is high, and the total yield is 33.6% and higher than that of an existing production process; and operation is convenient, reaction post-treatment is easy, column chromatographic purification is not needed, and industrial batch production can be achieved.
Description
technical field [0001] The invention relates to the technical field of medicine preparation, in particular to a method for synthesizing optically pure cloprostinol. Background technique [0002] Prostaglandins (PGs) are a class of important endogenous substances with a wide range of physiological activities. Each of the compounds has the same parent structure, and the main difference is the difference in the structure of the upper and lower side chains connected to the parent structure. Cloprostenol, the English name is: Cloprostenol, the molecular formula is: C 22 h 28 ClO 6 . In October 2003, the Ministry of Agriculture approved cloprostinol for injection and its sodium salt as a new veterinary drug. Cloprostinol recorded in "Chinese Veterinary Pharmacopoeia" is a mixed-rotational compound, and the difference in the structure of the left-handed and right-handed compounds in the mixed-rotational compound is the difference in the chiral configuration of the lower side c...
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IPC IPC(8): C07C405/00C07D307/935C07C211/27C07C209/00
Inventor 郑飞剑李刚万明魏积福石小伟吴进泉张江平刘斌福郭玉强赖育来李娟李迎春陈思涵张立军王萍
Owner 厦门欧瑞捷生物科技有限公司